There are some markets that you may be able to make a purchase with what you have available. 

It would be unfair for me to give any kind of general satisfaction/unsatisfaction because there is still a lot ahead to be determined.A quick snapshot:-Purchased lot in February 2022.  

If so, then you would want to purchase a homeowner's policy.  

Help him purchase another home Subject to that existing mortgage. 

You can save a lot on costs if you do many repairs yourself.Look into hard money lenders or private lenders for the initial purchase and rehab.Connect with wholesalers, agents specializing in investment properties, and other BRRRR investors to find deals and learn more.

The reason to have comparables is if you are representing someone or perhaps purchasing a house for yourself to live in.

You can also assess a dollar amount that you value the cost of these requests to be, and ask for these as a discount from the purchase price or a concession to you for closing costs. 

This would allow you to sell a property you had purchased with the intent of holding for productive investment use. 

Congrats on your lot purchase in an awesome Chicago neighborhood like Humboldt Park.

I'm considering purchasing a condo or a small SFH in the Oceanside/Carlsbad area as an investment property and renting it out on a short term rental site like AirBNB.